Get Smart (1965)

S5E4 Widow Often Annie

Chief assigns Max the task of wooing and marrying Ann Cameron, an alluring widow rumored to have killed her twelve husbands for their insurance payouts, which she generously contributes to KAOS. The planned wedding happens to fall on the occasion of The Smarts' first anniversary, causing frustration for 99 as she grapples with the unexpected overlap of the two significant events.